Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Radical Reactivity: Overview

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...

Radical Reactivity: Nucleophilic Radicals

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

Radical Formation: Elimination

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...

Radical Reactivity: Steric Effects

Radical Reactivity: Steric Effects

The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic factors, steric factors also account...

Radical Substitution: Allylic Chlorination

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Practical and divergent electrochemical access to thiocarbamoyl fluorides and N-trifluoromethyl amines from secondary amines.

Nature communications·2026

Same author

Electrochemical Trideuteromethylation with AcOD-<i>d</i><sub>4</sub>: A Route to CD<sub>3</sub>-Labeled Building Blocks.

Organic letters·2026

Same author

Probing cognitive reserve with resting state functional connectivity in subcortical ischemic vascular cognitive impairment.

Journal of Alzheimer's disease reports·2026

Same author

Hexahydroquinoline Featuring Amide Functionality: A Promising Scaffold With Calcium Channel Blocking Activity.

Drug development research·2026

Same author

eCyclopropanation - a safe and scalable electrochemical route to cyclopropanes.

Chemical science·2026

Same author

Azithromycin in preterm premature rupture of membranes: population pharmacokinetics and dose optimization.

American journal of obstetrics and gynecology·2026

Search research articles

Related Experiment Video

Updated: Jul 4, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Using toluates as simple and versatile radical precursors.

Kevin Lam¹, István E Markó

¹Département de Chimie, Bâtiment Lavoisier, Université catholique de Louvain, Place Louis Pasteur, 1, B-1348 Louvain-la-Neuve, Belgium.

Organic Letters

|May 30, 2008

Summary

The toluate group can be used as a radical precursor in chemical reactions. This study explored its use in deoxygenation and cyclization processes.

Area of Science:

Organic Chemistry
Radical Chemistry

Background:

The toluate moiety is a functional group derived from toluic acid.
Radical precursors are essential for initiating radical reactions.

Purpose of the Study:

To investigate the utility of the toluate moiety as a precursor for radical generation.
To explore the application of toluate-derived radicals in deoxygenation and cyclization reactions.

Main Methods:

Studied deoxygenation reactions involving the toluate moiety.
Investigated cyclization reactions utilizing radicals generated from the toluate group.

Main Results:

Demonstrated the successful generation of radicals from the toluate moiety.
Showcased the effectiveness of these radicals in promoting deoxygenation and cyclization.

More Related Videos

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Related Experiment Videos

Last Updated: Jul 4, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Conclusions:

The toluate moiety is a viable precursor for radical generation in organic synthesis.
Toluate-derived radicals offer a useful pathway for deoxygenation and cyclization reactions.